Hurt when head is broken outside city (5)
I believe the answer is:
ached
'hurt' is the definition.
(I've seen this before)
'head is broken outside city' is the wordplay.
'is broken' is an anagram indicator.
'outside' is an insertion indicator (some letters go outside others).
'city' becomes 'c' (this could be a standard abbreviation which I don't know about).
'head' is an anagram of 'ahed'.
'ahed' enclosing 'c' is 'ACHED'.
'when' acts as a link.
Can you help me to learn more?
(Other definitions for ached that I've seen before include "Yearned" , "Throbbed" , "caused discomfort" , "suffered" , "Hurt" .)